Synthesis 2020; 52(22): 3295-3325
DOI: 10.1055/s-0040-1707884
review
© Georg Thieme Verlag Stuttgart · New York

Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules

,
School of Chemistry, Trinity College Dublin, The University of Dublin, Trinity Biomedical Sciences Institute, 152–160 Pearse Street, Dublin 2, Ireland   eMail: sengem@tcd.ie
› Institutsangaben
This work was supported by a grant from Science Foundation Ireland (SFI IvP 13/IA/1894).
Weitere Informationen

Publikationsverlauf

Received: 02. April 2020

Accepted after revision: 12. Mai 2020

Publikationsdatum:
03. Juli 2020 (online)


Dedicated to Prof. Dr. Henning Hopf

Abstract

The remarkable structural and electronic properties of rigid non-conjugated hydrocarbons afford attractive opportunities to design molecular building blocks for both medicinal and material applications. The bridgehead positions provide the possibility to append diverse functional groups at specific angles and in specific orientations. The current review summarizes the synthetic development in CH functionalization of three rigid scaffolds namely: (a) cubane, (b) bicyclo[1.1.1]pentane (BCP), (c) adamantane.

1 Introduction

2 Cubane

2.1 Cubane Synthesis

2.2 Cubane Functionalization

3 Bicyclo[1.1.1]pentane (BCP)

3.1 BCP Synthesis

3.2 BCP Functionalization

4 Adamantane

4.1 Adamantane Synthesis

4.2 Adamantane Functionalization

5 Conclusions and Outlook